Ep 137 Career: The Pros and Cons of Going Out on Your Own

Show notes

What’s going on, everybody? Welcome to the 137th episode of The Crazy One Podcast.

I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design, and everything else that matters to creative people.

If you like what you hear, do me a favor:

Tell a friend. Leave a review. Share it.

Because we’re in a moment where a lot of people could use honest advice. That’s what this episode is all about.

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Three Years on My Own – What I’ve Learned

Almost three years ago, I got laid off—for the third time in my career.

And what followed was one of the most eye-opening and transformative journeys of my life. I went from job hunting to starting my own design studio, CRZY Design. What began as a way to pay the bills became a mission, a calling, and a completely new way of living and working.

In this episode, I want to walk you through that journey:

• The truth about how it started

• The real pros and cons

• What I’ve learned—and what I wish I’d known sooner

 

If you’re thinking about doing something similar, this one’s for you.

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The Beginning: No Grand Plan

Let me be honest—I didn’t start my business with a master plan.

When I got laid off, I was disheartened but determined. I told myself I’d reclaim my power, get back out there, and find a new role.

I thought I’d be documenting my triumphant return to full-time work.

Instead, I ended up documenting months of no traction—bad interviews, empty promises, and roles that just didn’t fit. It was demoralizing.

What I didn’t realize at the time was that I was experiencing the early signs of the design industry’s contraction—the devaluation of design, leadership, and creativity that’s only gotten worse.

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From Freelance to Founder—Reluctantly

Freelance started as a way to pay the bills. I resisted making it anything more. I had a million excuses:

• It’s not secure

• I don’t want to deal with the business side

• I’ve always been in-house or at an agency

• I don’t want to mess this up

 

But then, two of my clients said the thing that changed everything:

“If you’d commit to doing this full-time, we’d keep you on retainer.”

That was the turning point. And it wasn’t glamorous or cinematic. I didn’t get funding. I didn’t take out a loan.

I just started—built something real from the ground up.

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Let’s Talk About the Cons

Let’s start with the tough stuff—because it’s real.

1. You Have to Do Everything

Business insurance. Taxes. Contracts. Invoicing. Chasing payments. Setting up your S-Corp.

I didn’t go to art school to do this stuff. But it’s part of the deal.

2. Uncertainty Is Constant

There’s no safety net. No “blame the boss” when things go wrong. If it fails, you own the failure. That’s hard—but also freeing.

3. Vulnerability Is Inevitable

Putting yourself and your vision out there, betting on your taste and ideas—it’s scary. Especially when you’ve spent years being institutionalized by corporate systems.

But the biggest con?

For the first time, there’s no one else to blame.

If it doesn’t work, everyone knows who screwed up.

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But Then—The Pros

Now let’s talk about what’s been amazing. Because there’s a lot.

1. I Love What I Do Again

I wake up excited to work. I look forward to what I get to create.

I’m not surviving the day anymore—I’m living it.

2. I’m Proud of My Work Again

After years of work I wasn’t proud of, I now do work that matters to me.

I’m behind on posting case studies because I’m busy doing actual work that excites me.

3. I Found My Creativity Again

I was told for years to “stay in my lane.”

Now? I get to do strategy, branding, AI, apps, events, and more.

That variety is my strength.

4. It’s Financially Working

Last year was my most financially successful year ever.

And I did it without burning myself out too badly (okay, I worked 7 days a week—but I loved it).

5. I Regained Control

No more waking up to find my future decided by some boardroom deal.

I have my own boat now. And I’m the one steering it.

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The Moment That Changed Everything

There was one simple moment that made me realize things had shifted.

Every morning used to start with:

“How do I survive today?”

Now, every morning starts with:

“What amazing stuff do I get to make today?”

That one difference has changed everything—my creativity, my mental health, my marriage, my confidence.

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The Truth About Starting Your Own Thing

If you’re thinking about going solo, here’s the truth:

• You’ll question yourself.

• You’ll feel fear and imposter syndrome.

• You’ll worry about money, clients, and your family.

 

But if you push through?

If you bet on yourself?

If you can rediscover what you actually want?

It might just be the best decision you’ll ever make.

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Final Thoughts

I’m not saying it’s easy.

I’m not saying it’s for everyone.

But I am saying this:

You are more capable than you think.

You are not too late.

You are not stuck.

You are not crazy to want something different.

If you’re tired, frustrated, or feel like your talent is being wasted, listen to that voice.

Ask yourself the hard questions.

Figure out what you really want.

Then take the first step.

You might just find your way back to loving what you do.

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If this resonated with you, let me know.

DM me. Email me. I’ll do a Q&A. I’ll go deeper in another episode if you want.

Because if you’ve made it this far into this episode, I know something in you is stirring.

And maybe now’s the time to do something about it.

And as always—stay crazy.

Tagged as:
agen betting on yourself business advice career change creative business creative careers creative entrepreneurs design leadership entrepreneurship freelancing navigating uncertainty personal growth starting your own business work fulfillment